


Simple Man

by njgirl0976



Category: Supernatural
Genre: 'Cause sex happens, Dean sings like Jensen, Dean sings songs Jensen has sung for us, Did I mention sex?, Drinking, Emily is based on a real Emily, F/M, Flirting, Guitars are sexy, Guitars played by Dean Winchester are sexy, I love the way Jensen sings, I need to stop with these tags, No Sam Winchester, Sam's the main Winchester in my next fic, Sex, Singing, don't look at me like that
Language: English
Status: Completed
Published: 2016-03-22
Updated: 2016-04-09
Packaged: 2018-05-28 07:53:00
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 6,170
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6321217
Author URL: https://archiveofourown.org/users/njgirl0976/pseuds/njgirl0976
Summary: <blockquote class="userstuff">
              <p>Dean Winchester walks into her roadside dive bar, armed only with his guitar, a panty-melting smile, and a give ‘em hell attitude. Emily Hoskins wasn’t sure if someone that pretty could be that good of a singer or if he could handle the rough biker patrons of her place. Dean only has a single chance to prove himself worthy of the $200 Emily’s promised if he can survive one set.</p>
            </blockquote>





	1. Chapter 1

“Hey.”

Emily Hoskins looked up blearily from her mug of extra-strong black coffee. The guy standing in front of her was tall enough to make her crick her neck as she looked up at him. Emily blinked a few times to focus.

“Help--” Emily’s voice came out as a croak, so she cleared her throat hard before trying that sentence again. “Help you?”

The guy smiled and Emily rolled her eyes. Sunday mornings were the worst day to be into work early since Saturday nights were always seemed to last for 40 years, but Sunday was the only day Emily was able to get anything resembling accounting could get done, so here she was: in the bar at 9am with her laptop open in front of her and a week’s worth of tickets spread around her on the table, nursing a serious lack of sleep and a cup of coffee powerful enough to eat away the metal of spoon.

“I saw the sign out front,” the guy was saying. His voice was low and throaty with a little bit of a twang. “You still looking for a band?”

Emily tucked her wavy red hair behind her ears and motioned to the chair across from her.

“Sit down,” she offered. “You’re making my neck hurt.”

The guy sat down and Emily finally got a good look at him. Holy shit. He was gorgeous. Like model-gorgeous: sandy brown hair, freckles, lips that could only be described as bow-shaped, and his eyes. That wasn’t even right. Emily had never seen green eyes like his before. He smiled again and Emily swallowed hard. Nope, too pretty and too young. There was no way he’d survive here.

“Listen--” she began.

“Dean,” he interrupted, still grinning. “Dean Winchester.”

_Fuck me sideways,_ Emily thought. “Listen, Dean Winchester,” she continued. “I don’t think you’d work out here.”

Dean Winchester’s eyebrows drew together over those stunning green eyes as a confused look flashed over his face.

“You haven’t even heard me,” he said, his voice beginning to sound a little petulant. He looked up at her through long eyelashes ( _how did a guy get eyelashes that long?_ emily wondered), a little grin playing across his full lips. “How about if I play you something and then you decide?”

Emily made a face, crinkling her nose. If she let her hormones do the deciding, she would hire him on the spot without playing a note. But this was a rough and ready bar with an even rougher and readier clientele. Emily knew her patrons: they wouldn’t put up with some pretty boy with lips and eyelashes like a girl playing pop music on a guitar.

“Fine,” Emily answered as her entire being battled internally over this whole deal. “ _One_ song.”

Dean Winchester’s smile could have lit up the Chicago skyline. “Great. I’ll be right back.”

He got up off the chair and walked out of the bar. Emily watched him go. Not like she needed the confirmation, but Dean Winchester definitely had a sweet ass. Emily could see the sinewy muscles of his back move under the material of his flannel shirt.

“This is really bad,” Emily commented to herself and tried to go back to her books as she waited for Dean Winchester to come back in.

And, when he did, oh, did he _ever_ come back in. The creak and bang of the old door opening made Emily look up and her breath caught in her throat. Dean Winchester moved with the grace of a man comfortable in his skin. He strode back in on a pair of the sexiest bowlegs Emily had ever seen, swinging a battered guitar case in one hand, looking like he owned the empty bar. The door didn’t close behind him, letting in the weak March sunlight, which lit Dean Winchester up from behind like an idol. He jumped onto the stage like a pro, those long legs of his propelling him up with zero effort. Dean Winchester opened his case, pulled out a gleaming acoustic guitar, and perched one ass cheek on the stage’s lone bar stool. He started to tune up, plucking and adjusting, while Emily pretended to balance the bar’s accounts.

“What’s that?” asked a girl’s voice behind her.

Emily glanced over her shoulder at the petite brunette standing over her left shoulder. Ruby was the sassiest waitress Emily had ever met with the meanest right hook, a skill that was invaluable in their bar.

“That’s Dean Winchester and he wants to be our nightly entertainment,” Emily replied, turning back to the stage--no, back to her laptop.

“Huh,” Ruby mused as she sat down at the table next to Emily. “He can be _my_ nightly entertainment. And they’re gonna eat him alive.”

Emily’s eyes roved over Dean Winchester, who looked up suddenly, saw her looking, and grinned. Emily flushed red. Ruby wolf-whistled across the room at him.

“Hey, sexy!” she shouted.

“Hey,” Dean Winchester replied.

Ruby elbowed Emily. “He’s smokin’ hot.”

Emily nodded. “No shit.”

Dean Winchester cleared his throat and the girls stopped talking. He started to play the first few chords of Skynyrd’s _Simple Man_ before stopping and tuning again. Emily and Ruby both groaned.

“Jesus, not this fucking song,” Emily groaned, pinching the bridge of her nose between her thumb and forefinger.

It’s a well-established fact that drunk bikers and rednecks love _Simple Man_. No song is more overplayed in roadhouses than that one.

“I’m gonna go hide.” Ruby stood up and started to walk away as Dean Winchester started to play again.

And then … then he began to sing.

Dean Winchester had the most soulful voice Emily had ever heard. It caressed the lyrics of the classic tune, making Emily really feel that his mother had sat him down and doled out this homespun advice. Dean Winchester sang with his eyes closed and, when he opened them, he locked his eyes with Emily and didn’t let go.

“Holy shit,” Ruby said softly, coming back to the table to watch.

He played the song slower than the original version, almost like a love song. When he hit the last line of the second verse and growled out “And don't forget, son, there is someone up above,” Emily was sold.

Spellbound, Emily watched as Dean Winchester sang his heart out. He meant every word, using so much emotion and putting so much power into his voice that Emily honestly forgot he was by himself up there with just a guitar and not being backed by a five-piece rock band.

When he was finished and the last chord of the song had faded away, Emily swallowed again. She needed a shot. She needed two shots. She needed a whole bottle of whiskey. Ruby stared at her, waiting for an answer. On stage, Dean Winchester stared at her, his head cocked to the side, another one of those knowing smiles curling his mouth into a smirk. He knew he was good. He knew he was beautiful. And he knew he was hired.

Emily took in a deep breath and looked back down at her laptop, letting her red hair fall around her redder cheeks, as Dean Winchester jumped down off the stage and headed over to her table.

“Be back here at 9 o’clock, Dean Winchester,” she ordered, refusing to look at him.

Emily started transposing the totals from the receipts to her accounting program. She knew Dean Winchester was standing over her, waiting for her to make eye contact. When Emily didn’t give in and didn’t glance up, Dean Winchester laid his hand next to her arm. Emily flicked her eyes over as his index finger reached out ever-so-slightly to stroke her forearm. Just that light touch raised goosebumps all over Emily’s arms.

“Call me Dean,” he suggested softly, his voice dripping sex over the raspy tone like hot molasses.

The back of Dean’s hand was sprinkled with freckles and golden hairs that shimmered in the harsh overhead lights of the bar.

Emily finally raising her face to look at him.

Dean was gazing down at her, one eyebrow arched, lips pursed in a naughty smirk, eyes shining with a wicked gleam. Emily exhaled deeply. She hadn’t even realized she was holding her breath.

“Call me Emily,” she replied in a voice that betrayed her feelings with an embarrassing squeak.

Dean traced his finger down her arm to her hand before leaning over slightly to pick up his guitar case.

“See ya at nine, Em,” he said easily and he left.

Emily bit the inside of her cheek, trying to collect herself.

“Well,” Ruby said suddenly, snapping Emily back to reality, “I don’t see how this could end badly at all.”


	2. Chapter 2

Sunday night at the bar wasn’t the busiest night. That honor went to Saturday, but Emily never assumed that it was a going to be a quiet night. And this Sunday was turning into one of those weird-ass rare Sundays where everyone was fighting with their spouse and barging in the door, demanding booze.

It wasn’t until Emily checked her phone and realized it was 8.30 that she took a minute to assess the crowd. It was the usual motley crew of bikers and rednecks and barflys with more than a few hipsters and early 20s partiers here or there. Because the youngsters had discovered that coming to a roadside dive bar to laugh at bikers and drink cheap beer is more fun than paying for weak cocktails at Chilis.

“Hey, have you seen Dean?” Emily called over to Ruby.

Ruby slammed her tray down on the bar and yelled “Two Buds and two shots!” at Benny, the other bartender. Then she laughed in her boss’s face.

“You must be blind,” Ruby snorted. “He’s been sitting at the end of the bar, watching you, for an hour.”

“What?” Emily jerked her head toward Benny’s end of the bar and saw what Ruby was not to subtly pointing at.

Dean was sitting there, a bottle of beer in front of him. When he saw Emily was finally looking his way, he raised the bottle at her in salute before bringing to his gorgeous mouth. Emily tried not to stare as he sipped the beer, but the draw of watching his lips purse around the open end of the beer then the tip of his pink tongue taste the beer off his mouth was just too strong. Emily shook her head, put on her best manager face, and headed over to him as Ruby accepted her drinks from Benny.

“What’s goin’ on with the boss?” Benny asked in his thick Louisiana drawl.

Ruby laughed again. “Not much. Em wants to bang the help.”

“Not me, though?” Benny teased.

“Sorry, Bubba.” Ruby patted Benny’s hand. “It’s never gonna be you. Not after … _that_.”

Ruby motioned in Dean direction. Benny whistled, low and slow.

“Him?” Benny asked. “That sweet face I’ve been servin’ drinks at all night?”

“Yeah.” Ruby picked up her tray. “He’s the live act.”

Benny inspected Dean again like he was a side of beef. “He’s gonna entertain the sweaty masses tonight?” Ruby nodded and Benny let out a sharp bark of laughter. “That boy better know some rock n’ roll.”

The memory of Dean belting out Skynyrd that afternoon flashed across Ruby’s mind.

“He should be fine,” she said before walking away.

“How long have you been here?” Emily demanded when she reached Dean.

“Since about 7ish,” Dean replied. He set his half-empty bottle back down in front of him. “Place gets kinda busy on Sundays, huh?”

“Are you ready?” Emily asked, ignoring the way he was gazing at her. Her skin was prickling all over and she could feel the heat rising up her neck to her face. “You’re on at 9.”

“I thought you said get here at 9,” Dean teased lightly.

Emily rolled her eyes. “Well, you’re early. You gotta warm up or anything?”

Dean shrugged negligently. “I usually don’t.”

“You’re pretty fucking cocky, aren’t you?” Emily’s jangled nerves was making her more snappish than usual. Why was he getting under her skin so much? What made him so special?

_Well, he is ridiculously goddamn beautiful,_ her brain volunteered.

_Jesus, fucking focus, Emily,_ she scolded herself.

Dean stood up, tugging a little on the waistband of his jeans. Emily’s eyes immediately and inadvertently went to Dean’s long, calloused fingers, which he’d hooked through the belt loops.

“Oh, you know I’m fucking cocky,” Dean agreed, his voice low and oozing sex. The emphasis on ‘cocky’ wasn’t lost on Emily.

Ruby and Benny had inched closer during the conversation. Emily could feel them breathing down her neck.

“Will you just--will you just go get ready?” she snapped, waving her hand at the stage.

“We never talked about payment,” Dean said suddenly, licking his lips.

“Pay--?” Emily was caught off-guard. “Oh! Ummm--” She hated the way Ruby and Benny were staring at her and poking each other. She had to get Dean away from her. _Fast._ “200.”

“ _Dollars?_ ” Ruby choked as Benny’s jaw-dropped.

“No, seashells,” Emily said. “Yes. Dollars. _If_ they don’t boo you off the stage or throw bottles.”

“Bottles?” Dean’s unwavering confidence finally wavered. “Really?”

“They only did it once, brother,” Benny reassured him.

“And I think they only needed 15 stitches,” Ruby added.

“In their face,” Emily finished.

Dean’s face went white under his freckles as he looked back and forth between the three of them and Emily immediately felt bad for fucking with him. But then Dean grinned. Emily couldn’t help it: she grinned back.

“I can do this,” he said, his swaggering confidence back. He eyed Emily, green eyes roving over her lazily from head to toe. “For 200 bucks, I’d do most anything.”

Emily felt her knees go weak as she hooked her fingers under the edge of the bar to steady herself. “Get away,” she said, with more conviction than she felt. “I’m trying to ignore you.”

Dean laughed, then leaned toward the bar to grab his beer and take one final pull off it.

“Sweets,” he said, dropping his now-empty bottle on the bar, “you couldn’t ignore me if you tried.”

“Oh, my god. Shut up.” Emily grabbed the bottle and walked away as she grinned to herself. Dean had quoted _The Breakfast Club_ at her.

But, fuck, if Dean wasn’t right as hell. Emily leaned against the bar to admire him as he strolled up to the stage. That man was sex on bowlegs and there was no denying it. Emily started to wonder what he was like in bed. Guys that hot were never that great in the sack. Overly-confident in their own good looks, it usually made them think they didn’t have to put any effort into sex. Emily kinda hoped she could find out of that preconceived notion was true or not.

“Hey, I’m Dean,” Dean was saying into the microphone.

The bar didn’t quiet down much, but Dean’s good looks did catch the eye of the people closest to the stage. There were a few hoots and whistles, which made him grin.

“Take off your shirt!” was one shouted suggestion, making the crowd--and Dean--laugh.

Dean strummed his guitar, barely tuning it before starting the first chords of _Stairway to Heaven_. Emily stopped working to watch him. Next to her, Benny cringed a little.

“He’s starting with _that_?” he asked. “That’s bold.”

“This should be interesting.” Ruby joined her coworkers, leaning on the bar on her elbows. “If nothing else, he’s fucking pretty.”

“Shh!” Emily heard herself hiss.

Behind her, Benny and Ruby exchanged identical smirks.

Dean started slow with _Stairway_ , as was expected with that song. The bar started to quiet a little more and a little more as the song grew. Emily, Benny, and Ruby watched in awe as the rowdy rednecks and bikers grew less interested in their antics and more interested in the guy playing Led Zeppelin.

When Dean reached the bridge, Emily couldn’t take her eyes off of him. He was mesmerizing.

“Boss Lady, look at ‘em.” Benny dug his elbow into her side.

Emily tore her eyes away from Dean to glance around the bar. They were into it. _Really_ into it. Nodding their heads, lip syncing along, audibly commenting “He’s fucking _good._.” But it was when Dean hit the last stanza and half the bar started singing along, Emily, Benny, and Ruby exchanged shocked looks.

“And as we wind on down the road/Our shadows taller than our soul/There walks a lady we all know/Who shines white light and wants to show,” Dean howled into the mike with a decent amount of patrons as his back-up singers.

“What the fuck is happening here?” Emily asked, astounded.

“Am I in the _Twilight Zone_ , seriously?” Ruby asked.

Dean barely let the applause die down before he launched into The Allman Brother’s _The Midnight Rider_. That choice brought a raucous cheer from the bikers and Dean shot them a “Yeah, brother” over the mike.

“Hey, can I have a beer?” asked a voice.

Emily shoved Benny toward the voice without taking her eyes off Dean. Benny rolled his eyes, handed the customer a beer, and went back to work, leaving Emily to gaze dreamily at Dean.

“Yo, heart eyes,” Benny said after a while, nudging her. “You wanna give the guy a break? He’s been playing for almost 45 minutes.”

Emily shook her head “no” without blinking. “Another 15.”

“An hour straight?” Benny asked.

Emily waved her hand over the bar crowd. “Look at them. If I make him stop, they’ll riot.”

Dean ended his rendition of _The Weight_ with a flourish and was met with cheers, stomping feet, and dollars thrown on the stage like he was a stripper. He scooped up the money tossed at him, tucked his guitar behind him, and announced into the mike he’d be back in 15 minutes.

“Sounds like he’s giving himself his own break,” Benny commented mildly.

Dean made his way over to the bar and Emily felt a thrilled wave of excitement rush over her. God, he was like a rockstar, working his way through the crowd, accepting slaps on the back and handshakes like a pro. More than a few of the women were eyeing him up like a slab of meat. A few guys were too.

“Water?” Emily asked when he finally reached her.

“Please,” Dean said.

Watching Dean chug back a water was like porn to Emily’s over-wrought hormones. Once the bottle was empty, Dean licked his lips as he checked Emily out again, gazing at her through his long lashes.

“Anything you wanna hear next, Em?” he asked, twirling a drink straw between his fingers lazily.

Emily tried not to stare at his hands as she answered, “Your _Simple Man_ was pretty impressive.”

Dean half-smiled at her answer. “Is that a cross?”

Emily’s fingers flew to her necklace. The little cross that laid in the hollow of her throat was such a part of her, she didn’t even notice it any more. It didn’t mean much to her, religion-wise, but a gift from her long-gone grandma was too personal to get rid of. But there was no way she was telling Dean that, so Emily shrugged noncommittally. Dean smiled roguishly.

“Gotcha,” he said. Jamming the straw in the corner of his mouth, he winked at Emily. “Back at it. Really wanna earn that 200 bucks.”

“I bet you can think of a few other ways he can earn 200 bucks,” Ruby commented as she sidled up behind Emily.

“Fuck off,” Emily said immediately, making them both laugh.

Dean’s reappearance on stage was met with a rousing cheer. He pushed the stool out of the way and stood there for a minute, green eyes scanning the bar. Emily caught his glance and he winked at her. Emily glanced away for a second, then back again. Fuck it. She winked back. Dean looked her up and down, then turned his attention back to the microphone.

“You guys all know Emily?” he asked. A couple bar patrons hooted and most of them looked Emily’s way. Emily waved sarcastically, then flipped her middle finger at them, earning an appreciative laugh from the crowd. “Well, Em’s asked me to do a song that’s near and dear to her heart.” Dean pulled his guitar in front of him and rolled his shoulders to re-adjust the strap.

“ _Simple Man_?” Ruby asked as she picked up a couple bottles of beer.

Emily shrugged. “Probably.”

Dean plucked out the opening chords of a song that Emily didn’t recognize right away. He bit his bottom lip, suddenly playing shy, leaned close to the mike, and breathed out the first line of Night Ranger’s epic _Sister Christian_ :

“Sister Christian, oh the time has come. And you know that you’re the only one to say ... okay.”

Emily knew she looked confused. “I don’t get it. Why _Sister Christian_?”

Benny let out a sudden laugh. “Boss Lady, what do you wear around your neck?”

Ruby leaned across the bar and flicked the cross dangling off its chain.

“Sounds like he has a good girl kink,” Ruby said as she walked away with her tray.

“Well, I’m anything but,” Emily commented to the empty air around her, but didn’t take her eyes off Dean.

“Girl, you need to bang that,” a voice said suddenly.

“What?” Emily started and turned to face one of the regulars.

The woman grinned at Emily with her cigarette-stained teeth before jerking her thumb over her shoulder at Dean Winchester.

“That. You need to bang _that_ ,” the woman repeated.

Emily shook her head, half-smiling at the insistence in the woman’s voice.

“Yeah, I’ll think about it,” she agreed.


	3. Chapter 3

**Notes for the Chapter:**

> Oh, no! Sex! Cover your eyes!

To say Dean was a hit was a total understatement. He closed out his set with an even more passionate version of  _ Simple Man _ that had a few drunk bikers crying into their beers. The amount of dollars he had thrown at him would have made Vegas strippers jealous.

Dean sprawled himself across on the corner bar stool for the rest of the night, refusing drinks and phone numbers and offers of quickie sex in the bathroom. He was adorable and sexy and gracious and flirty and utterly edible. Emily knew he was watching her and she tried desperately to ignore that fact, but kept finding herself looking his way.

“Boss Lady, you stare at that boy any harder and his clothes’ll fall right off,” Benny commented mildly at one point.

“That’s what I’m hoping for,” Emily told her bartender.

When last call rolled around, Dean had been done singing for about two hours and had been offered beers by most everyone who came up to him. Dean turned them down graciously, saying he had to drive that night and he had no intention of cracking up his Baby.  Emily assumed that “Baby” was what Dean called his car. Bikers who would usually throw a punch if their drinks were refused were so dazzled by this green eyed and freckled supermodel that they just pressed the booze money into his hand and told him he needed to record an album.

Ruby and Benny hung around way longer than they usually did while Emily counted out the tills, setting aside Dean’s well-deserved $200. The bartender and the waitress nudged each other a few times, watching Emily as she stacked the 20s neatly in a pile.

“What the hell are you two still doing here?” Emily asked them. “You’re usually long-gone by now.”

“Oh, nothin’, Boss Lady,” Benny answered.

“We just wanted to keep you company,” Ruby agreed, all innocence.

Emily rolled her eyes. “Y’all need to get out of here.”

“You sure, Boss Lady?” Benny asked, putting on a concerned face. 

“Get lost, you two,” Emily ordered.

Benny and Ruby gathered their things, nudging each other and rolling their eyes comically at Emily. Annoyed, Emily held the door open for them as they left. Benny paused, leaning back in the doorway at the last second.

“Sure you don’t want me to stay?” he asked, wiggling his eyebrows.

Emily pushed him out of the door by his face. “Get lost, swamp-rat.”

She could hear Benny’s pirate-like guffaws as she locked the door after him. When she turned back around, Dean had moved his seat closer to where Emily had been doing the close-up paperwork. Emily’s heart thumped a little. Maybe she was a little too swift in getting rid of Benny. What if this charming and sexy stranger robbed her? There was easily a few thousand dollars in piles on the bar in front of him. Emily straightened her shoulders and headed back over to him, readying herself for whatever--if anything--Dean had planned.

“You still here?” Emily asked as she walked towards him. 

“I am,” Dean replied, his pink tongue peeking from between his straight white teeth.

Emily and Dean fell silent for a minute, eyeing each other appreciatively.

“You always close up by yourself?” Dean asked. His voice was low and rough from singing all night and it sent a shiver down Emily’s spine. “All this money and you all alone? That really so safe?”

Emily knew he was flirting and she knew she shouldn’t respond to it because she was an adult and it was beneath her to play coy with a stranger in the bar because her whole life was strangers in the bar but oh, my fucking god, he was so goddamned pretty and his lips were so goddamned kissable and it had been way too goddamned long that Emily grabbed the front of Dean’s open blue shirt in her fists and kissed him. Hard.

And it was everything Emily hoped it would be.

Dean’s hands went immediately to Emily’s face, cupping each cheek, fingers tangling themselves in her hair. His lips were plush and soft, but firm, against hers as his tongue pushed its way into her mouth. Emily let go of Dean’s shirt, gripping the back belt loops of his jeans, pulling his hips close to hers. She could feel him hardening through his jeans, so she wiggled herself against the bulge.

“Bad girl,” Dean whispered when their lips parted.

“You got no idea,” Emily shot back.

Dean started to walk Emily backwards to the closest table. Emily knew he was going to try to pop her up there and continue the make-out, but there was no way she was taking the chance of the rickety-ass bar table collapsing under her.

“Wait.” Emily pulled herself out of his arms and grabbed his wrist. “Follow me.”

Emily led Dean to the bar office, a dingily-lit hole in the wall room with an unused desk and a pull-out couch.

“A couch bed?” Dean teased as Emily opened it up.

Emily shrugged, suddenly aware of how musty the sheets on it smelled. “Serves its purpose.”

“Damn straight,” Dean agreed before pulling her against him again.

Dean buried his lips against her neck this time, moving his mouth down her throat to her collarbone, which he nipped lightly. His hands started finding their way into the openings of Emily’s clothes. Emily gasped, her breath shaky, as Dean’s fingers brushed over the bare skin. He pulled his mouth off her neck for a second to pull her t-shirt over her head. 

“You now,” Emily tugged Dean’s shirt. 

Dean grinned and stripped off his shirt. He was all lean, sinewy muscle and freckled shoulders. Emily licked her lips as she arched one eyebrow. Her fingers began to work his belt buckle before Dean could pull her against his chest. He held his hands up in the air as Emily yanked the belt out of the loops on his jeans with a flourish. Dean grinned roguishly at her as Emily undid his jeans and pushed them and his boxer briefs down.

“What about you?” he teased.

“Shut up and get on the bed, Winchester,” Emily ordered, sounding way more confident than she felt.

Dean sprawled across the bed, legs spread, hands folded behind his head. Emily stood at the foot of the bed and shimmed out of her jeans, tossing them and her bra to the floor. Without ceremony, Emily crawled up between his thigh and licked a long stripe up the underside of Dean’s thick cock.

The groan Dean let out spoke volumes about how good he thought that felt. Emily knelt up and swirled her tongue around the head before swallowing the length of him down as far as she could handle. Dean groaned again as Emily worked her mouth up and down his cock, pressing his hips against the mattress so he would stop thrusting up and choking her with it.

“Holy shit, Em,” Dean panted, clutching the sheets in his fists.

Dean’s body strained against Emily’s grip, writhing and bucking, until Emily could tell he was closer than he wanted to be to cumming. She slid her mouth up to the head and teased the opening with her tongue a little.

“Want me to stop?” She asked.

Dean lifted his head to meet her gaze. His green eyes were glassy, pupils blown out with lust.

“Unless you want me to cum,” he replied hoarsely.

Emily lapped his cock one last time. “Oh, hell no.”

“Get up here, bad girl,” Dean said.

Emily moved up to the head of the bed to lay next to him, but found herself on her back with Dean yanking her panties off and jerking her pelvis against his lips. She gasped as Dean’s mouth moved against her folds.

“My turn,” he breathed.

Dean buried his mouth between her lips, his tongue immediately finding her clit. Emily let out a high-pitched whimper as that beautiful mouth of his worked her. Gently at first, then harder and faster, Dean sucked and licked her sensitive nub as Emily’s legs tightened on either side of his head. Dean lifted Emily’s hips off the mattress, sliding his arms up underneath her to grasp her breasts. Rolling her nipples between his rough fingers, Dean teased her more.

“Fuck! Holy fuck! Oh, god, Dean. Don’t stop!” Emily begged, whimpering.

Rolling her hips against his mouth, Emily could feel an orgasm building. If that bastard kept eating her out like this, it wasn’t going to be long--

“Dean!” His name ripped from Emily’s throat as she came hard.

Dean hummed against her, licking her clean while Emily’s body shook from the force of her orgasm. He looked up at her, his green eyes surprisingly hopeful.

“Yeah?” He asked quietly.

“Holy fuck, yeah,” Emily panted.

Dean slid up the bed to lean against his elbow and look down at her. He looked so innocent for some reason, Emily had a hard time believing he’d just made her cum so hard, she was still having aftershocks. Emily sat up and pushed him onto his back so she could straddle his hips. Dean grinned up at her, innocence gone. 

“There’s a condom in my jeans pocket,” he told her.

Emily retrieved the condom and rolled it onto his cock slowly, loving how hard he was still, before lowering herself down on his impressive length. They both groaned as she bottomed out. 

“Not yet,” Dean said in a hushed voice. He took Emily’s hands in his, linking their fingers together. He gazed up at her, green eyes heavy-lidded with lust.

“Now?” Emily breathed, her body aching to feel him move inside her.

“Yes,” Dean whispered.

Emily began to move. God, he felt incredible. He moved against her, slow and sensual, filling every inch of her. Emily groaned, throwing her head back, moving faster. Dean thrust up, sitting up suddenly to wrap his arms around her waist and pull her mouth to his.

Kissing and nibbling as they moved together, Emily and Dean held each other close, arms tight around each other, Emily’s legs around Dean’s waist.

“Em, I’m close,” Dean suddenly gasped into her ear. Emily felt Dean’s hand between them, his fingers teasing her clit. “Cum with me, Em. Come on, sweetheart.”

Between Dean’s fingers and the deep, intense thrusts, Emily came hard again. She was cresting to a second orgasm when Dean stiffened underneath her and let out a cry as he came, gripping her close to him, fingers digging into her shoulder blades. Moaning, Dean rolled his hips lazily against Emily, prompting her to finish her second orgasm.

“Holy shit, Dean,” Emily whispered, laying her forehead against his shoulder.

Dean kissed her neck silently in response as his body shuddered against hers.

Emily rolled up onto her elbows and watched Dean pull his jeans up over his narrow hips. He got dressed just as sexily as he did everything else and Emily was loathe to see him put his clothes back on.

“Where you off to now?” She asked.

Dean shrugged as he slipped his grey t-shirt over his head. “Dunno. Maybe head up north and see if I can find work.”

“Work? You?” Emily asked. “Shouldn’t you head out to LA and become a big rock star?”

Dean paused before flicking the collar of his jacket straight. He snorted.

“Have you ever been to LA?” He asked. Emily shook her head, embarrassed. “Have you ever been  _ anywhere _ ?” Dean asked next. When Emily didn’t reply, Dean shook his head, his face dark and his eyes bitter. “Yeah, well, guitar players are a dime a dozen in LA. I’ll get out there and end up being an escort and fucking rich old ladies.”

Emily grinned, hoping to lighten the mood. “You’d be worth every penny.”

Dean looked her way, saw her smile, and let out a laugh. “Smart ass.”

Emily watched silently as Dean pulled on his boots and patted his pockets to feel for his wallet and keys. He looked like he was about to make a run for it, before he stopped himself abruptly. 

“Hey,” Dean said, sitting down on the bed next to Emily. He traced his fingers down her naked spine to the small of her back, where he rested his warm, calloused hand. Emily looked up at him, struck again by how beautiful he was. “Thanks for the job.”

Emily couldn’t stop her grin. “Thanks for the sex.”

Dean let out another laugh. “My pleasure.”

“Oh, mine too,” Emily bantered.

Dean leaned over and kissed Emily softly on the mouth, lips gentle, tip of his strong tongue flicked out to taste her top teeth. His fingers tightened on the small of her back, squeezing lightly. His other hand traced Emily’s jawline, coming to rest under her chin, so he could raise her face up slightly. 

_ God, can he ever kiss,  _ Emily thought distractedly.

When their lips parted, Dean pulled back. Emily opened her eyes, feeling light-headed.

“I better go,” Dean whispered. “Before you make it harder for me to leave.”

“You can stay,” Emily offered wildly. She cringed as soon as the words came out of her mouth. “Ugh. I am  _ such _ a girl.”

Dean smiled, standing up. “See ya around, Em.”

And then he was gone, closing the office door after him silently. Emily rested her cheek on her folded arms and stared at the door, wondering idly if Dean would walk back in and declare there was no way he could leave her. When Dean didn’t reappear, Emily closed her eyes, a smile playing across her mouth.

The money.

Emily’s eyes popped open. All the takings for the night were still spread across the bar. Jumping off the couch bed, Emily grabbed the first article of clothing she could find--Dean’s blue button down shirt--and threw it over her naked body as she ran into the bar.

Skidding to a stop, Emily saw the cash still in tidy piles on the bar top, minus the stack of 20s that equaled Dean’s pay for the night. Next to the bills was a white napkin with this written on it:

_ Thanks for the $200. You should probably lock the rest of this up.  _

_ See ya, Em. _

_ D _

Emily pulled the blue shirt, which still smelled like Dean, closed around herself, smiling. He knew how to make an entrance  _ and _ an exit, this guy.   



	4. EPILOGUE

*** Six Months Later ***  


“Hey! Boss Lady!” Benny yelled over the din of the crowd. 

Emily didn’t look up from the line of beer bottles she was uncapping. “What?”

“There’s a guy here, asking if you’re hiring guitar players.”

Emily jerked her head up and spun around. 

Dean Winchester was leaning against the bar, grinning that panty-melting smile at her.

“Hey, Em,” he said.

Emily felt her cheeks go pink. “Hey, Dean.”

“Nice shirt.” Dean nodded at his blue button-down she was wearing.

“This old thing?” Emily replied, pulling at the collar. “Some guy left it here.”

Dean grinned. “Maybe you should give it back to him.”

“Maybe he should earn it back,” Emily suggested.

“Any ideas how he can do that?” Dean asked.

Emily shrugged with one shoulder, smiling coyly. 

“Do you know  _ Simple Man _ ?” Emily replied.


End file.
